3 Tips for Exploring the St. Augustine Historic District

You can’t go to the oldest continuously inhabited city in the continental United States without spending a day or three in its Historic District.  This history-rich, architecturally fascinating section of town is packed with things to do for visitors of all ages. 

3 Tips for Exploring the St. Augustine Historic District

Here are three tips to help you strategize your next visit to historic St. Augustine.

Clang, Clang, Clang Went the Trolley

We’ve said it before but it’s worth repeating.  When a tourist destination is packed with things to see and do, so much so that it seems a bit overwhelming at first, start with a trolley tour.  It’s a great way to get a lay of the land and hear about the history, locations and activities available from an expert guide.  

When you’re done you can decide what interests you the most and head back to your favorite spots for closer inspection.  Or if you prefer, at least in the case of the St. Augustine Old Town Trolley Tour, get off at the stop of your choosing to spend a little extra time and then grab the next trolley.  They run about every 15 minutes.

We recommend you start the tour at the Old Jail.  There’s ample space here for parking, and plenty of things to do before jumping on.  There are 23 stops in total – not all of which are in the Historic District. But the trolley snakes back and forth so much the majority of the time is spent in the heart of the original city.  The tour is just shy of 90 minutes long, the entirety of which you’ll be entertained with stories from the city’s rich history to present day. 

Our tour guide’s name was quite literally Davey Jones, which opened the door to plenty of pirate (and Monkees) humor.  Queue a “Hey Hey We’re the Monkees” sing-along with the entire trolley. All in all it was a comedic and informative tour which set the table perfectly for the rest of our day.

The Old Jail, our recommended first stop is located at 167 San Marco Ave St Augustine, FL 32084 and the trolley runs daily from 9AM to 4:30 PM.  There’s plenty of ticket options that include admission to other attractions.  Visit the Old Town Trolley website for details.

3 Tips for Exploring the St. Augustine Historic District

Pirates, Treasure Chests, and Johnny Depp

We decided to make our first stop in the historic district the St. Augustine Pirate & Treasure Museum.  The museum uniquely combines the history and artifacts of pirates from St. Augustine’s past with a more modern look at the subject in film.

They made the extra effort to make this a real kid pleasing experience with interactive displays.  Our kids enjoyed guessing the contents of a cargo hold just from the scent, which is not nearly as gross as it sounds.  Another favorite activity was the cannon firing simulation, where we pretended to light up the gun powder, complete with big boom.  And have you ever seen a real pirate treasure chest?  We did and were fascinated.

The inclusion of props, posters and other info about pirates on the silver screen really topped off the museum tour.   From Errol Flynn, to Johnny Depp, if a movie included pirates its likely to be represented here. The centerpiece of the exhibit was a sword brandished by the infamous Jack Sparrow.

The St. Augustine Pirate and Treasure Museum is located at 12 S. Castillo Drive St. Augustine, FL 32084 and is open daily from 10AM to 7PM.

3 Tips for Exploring the St. Augustine Historic District

Eat your Way Through History

You won’t want to leave the St. Augustine historic district without taking advantage of some of its many culinary options.   There are a number to choose from, all within quick walking distance the pirate museum.

Why not continue your history-themed day and visit some places that perfectly tie in?  The Spanish dominated the area on and off for the first several hundred years of the city’s existence.  Taberna del Caballo is an authentic Spanish restaurant that’s located in a historic “taberna”, or indoor market place.  We enjoyed the empanadas! 

Did you know that the British occupied St. Augustine from 1763 to 1784?  It’s called The British Period and came about through the Treaty of Paris.  To celebrate head to the Bull & Crown Publick House in the Colonial Quarter for authentic British atmosphere and fare.  Another historic location, the Bull & Crown was built on the original site of a skilled Minorcan carpenter, Francisco Pellicer.  Grab a draught brew or a flight from the St. Augustine Distillery with some Fish & Chips!

Finally, you can’t go to a great coastal location like St. Augustine without sampling the seafood.  We suggest the St. Augustine Seafood Company.  In their own words, “We hope to share with you the story of St. Augustine’s proud fishing legacy by showcasing the people and history behind the rise of America’s shrimp boat city.”  If locally sourced seafood is what you’re after, this is the place to go.  Try the chowder, a seafood basket or fresh catch sandwich.

Disclosure: Thank you to St Augustine for hosting me and my family. Opinions here, as always, are all my own.

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